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Aziridine Termination of Living Anionic Polymerization
Author(s) -
Thomi Laura,
Wurm Frederik R.
Publication year - 2014
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201300860
Subject(s) - aziridine , tosyl , anionic addition polymerization , polymer chemistry , chemistry , carbanion , polymerization , living anionic polymerization , nucleophile , end group , polymer , amine gas treating , epoxide , copolymer , organic chemistry , ring (chemistry) , catalysis
A switch from carbanions to aza‐anions is performed by the addition of N ‐tosylaziridine (TAz) to living poly(styryl) (PS) chains. This is the first example of carbanionic aziridine ring‐opening which was previously activated by amidation with a tosyl group to enable nucleophilic ring‐opening by the living chain end. Poly(styrene)‐tosylaziridines (PS ‐ TAz) with narrow molecular weight distributions and variable molecular weights are synthesized. The removal of the tosyl group and subsequent functionalization is shown, evidencing quantitative transfer to azaanionic species. All polymers are characterized in detail by 1 H NMR spectroscopy, DOSY 1 H NMR spectroscopy, and size exclusion chromatography (SEC). This strategy allows the introduction of amine groups via anionic polymerization in analogy to the well‐established epoxide termination.